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From the body

DEA-NAEDocosatetraenoylethanolamide

Ethanolamide of adrenic acid, a brain cousin of anandamide, a poorly documented CB1 and CB2 agonist.

Endogenous
Level of detail

C₂₄H₄₁NO₂

CAS 150314-35-5

Family
Endocannabinoid or related mediatorPutative
Molar mass
375.60 g/mol

Updated on

In plain terms

Docosatetraenoylethanolamide is a small fatty molecule made by the body, a close cousin of anandamide with two more carbons. It was described in the brain, not in hemp, and it binds the same receptors as cannabinoids. Published work is scarce and there are no human data.

Receptors and activity

Target network

CB1AgonistKi = 253 nM · rat (recombinant receptor)COS cells transfected with the rat brain receptor cDNA; anandamide 155.1 nM in the same assay; another series: 34.4 nM (Reggio 2010)
  • Activates

The lower the cited value, the closer the target sits to DEA-NAE: one ring per factor of 100. A target with no measured value stays on the edge.

Where these targets live

Where each target has been found in humans, according to the cited studies. The map shows the target, not an effect of DEA-NAE.

Brain, side view
Body, front view
Blood

CB1CB1 found in 7 regions of the body

  1. Basal gangliadenseMost dense in basal ganglia outflow nuclei1
  2. CerebellumdenseVery dense in the cerebellum1
  3. HippocampusdenseVery high concentrations in the hippocampus2
  4. AmygdaladenseHigh concentrations in the amygdala2
  5. CortexpresentPresent throughout the neocortex2
  6. Adipose tissuepresentExpressed in adipose tissue3
  7. GutpresentColonic epithelium, smooth muscle and plexus4

Map sources

  1. Herkenham M et al. Cannabinoid receptor localization in brain. Proc Natl Acad Sci U S A, 1990 (new tab)
  2. Glass M et al. Cannabinoid receptors in the human brain: a detailed anatomical and quantitative autoradiographic study in the fetal, neonatal and adult human brain. Neuroscience, 1997 (new tab)
  3. Engeli S et al. Activation of the peripheral endocannabinoid system in human obesity. Diabetes, 2005 (new tab)
  4. Wright K et al. Differential expression of cannabinoid receptors in the human colon: cannabinoids promote epithelial wound healing. Gastroenterology, 2005 (new tab)

Cited values

  1. CB1AgonistKi = 253 nM · rat (recombinant receptor)43 out of 100

    Barg J. et al., Eur J Pharmacol 1995 (new tab) · COS cells transfected with the rat brain receptor cDNA; anandamide 155.1 nM in the same assay; another series: 34.4 nM (Reggio 2010)

  2. CB2Agonistno measured value cited
  3. TRPV1Agonistno measured value cited
Bar length follows the measured value (Ki, Kd, EC50 or IC50), on one scale shared by every entry, from 100 µM to 0.1 nM. A target with no cited value has no bar.

Pharmacology

Described in 1993 by Hanuš et al., docosatetraenoylethanolamide is the ethanolamide of adrenic acid (22:4 n-6), an anandamide lengthened by two carbons. Barg et al. (1995) measured in transfected cells a Ki of 253.4 nM and inhibition of adenylate cyclase with an IC50 of 116.8 nM, values close to those of anandamide in the same assay (155.1 nM and 100.5 nM), while another series reported in the review by Reggio (2010) gives 34.4 nM for this congener against 39.2 nM for anandamide: the protocols differ in scale and the gap has not been settled. The functional assays of Alharthi et al. (2018) place it, with anandamide, among the n-6 N-acylethanolamines that activate CB1, CB2 and the TRPV1 channel. In mice, Barg et al. observed all four responses of the cannabinoid tetrad: reduced motor activity in an open field, hypothermia, catalepsy and an antinociceptive effect. Beyond that work the literature is thin: physiological tissue concentrations are poorly documented and human data are lacking. Its status remains that of a putative endocannabinoid.

Key sources.

History

Source
An endogenous mammalian lipid, described as a brain ethanolamide (Hanuš 1993). It is not a phytocannabinoid: it appears in no profile of Cannabis sativa. Its parent fatty acid, adrenic acid (22:4 n-6), derives from arachidonic acid by chain elongation. The abbreviation DEA used in the lipid literature denotes this compound, not dehydroepiandrosterone.

Biosynthetic pathway

In vivo

The molecule follows the general N-acylethanolamine route, formed from a membrane N-acyl-phosphatidylethanolamide and then released by hydrolysis. No work specific to the biosynthesis of docosatetraenoylethanolamide was consulted in this audit: the description is that of the family, not a pathway demonstrated for this compound.

Classification

Family, origin and source verification

Family

Endocannabinoid or related mediator › Putative

Verification

Every fact on this entry was checked against its primary sources on 20 October 2026.

Wikipedia (English)

Docosatetraenoylethanolamide (new tab)

Article paired by the molecule's structure (InChIKey), revision read on 19 October 2026. Read as a second opinion, never cited as a source.

References

  1. Hanuš L., Gopher A., Almog S., Mechoulam R., Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor, J Med Chem 1993 (new tab)PMID 8411021
  2. Barg J. et al., Cannabinomimetic behavioral effects of and adenylate cyclase inhibition by two new endogenous anandamides, Eur J Pharmacol 1995 (new tab)PMID 8749028
  3. Alharthi N. et al., n-3 polyunsaturated N-acylethanolamines are CB2 cannabinoid receptor-preferring endocannabinoids, Biochim Biophys Acta Mol Cell Biol Lipids 2018 (new tab)PMID 30591150
  4. Sheskin T., Hanuš L., Slager J., Vogel Z., Mechoulam R., Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor, J Med Chem 1997 (new tab)PMID 9057852
  5. Reggio P.H., Endocannabinoid binding to the cannabinoid receptors: what is known and what remains unknown, Curr Med Chem 2010 (new tab)PMID 20166921
  6. PubChem CID 5282273, N-(2-hydroxyethyl)-7Z,10Z,13Z,16Z-docosatetraenamide (new tab)

Identifiers

Names

Common name
Docosatetraenoylethanolamide
IUPAC name
(7Z,10Z,13Z,16Z)-N-(2-hydroxyethyl)docosa-7,10,13,16-tetraenamide
Other names
N-docosatetraenoylethanolamine · DEA · NAE 22:4n-6

Identifiers

Formula
C₂₄H₄₁NO₂
CAS
150314-35-5
PubChem CID
5282273(new tab)
ChEBI
CHEBI:34478(new tab)
InChIKey
FMVHVRYFQIXOAF-DOFZRALJSA-N
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)NCCO

Machine-readable entry (JSON)

LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.